Hydrochloric Acid → N-benzyl-N-methylcarbamoyl chloride

HRID 1158436

Reaktionsgleichung

Reaktionsgleichung von HRID 1158436
N1C=CC=CC=1.[CH3:7][NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)(OC(Cl)(Cl)Cl)[O:17][C:18]([Cl:21])(Cl)Cl.Cl>C(Cl)Cl>[CH2:9]([N:8]([CH3:7])[C:18]([Cl:21])=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7669N-MethylbenzylamineHCID 94429Triphosgene

Produkt 1

HCID 10464985N-benzyl-N-methylcarbamoyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

At −78° C. pyridine (1.25 mL, 15.5 mmol) followed by methyl benzylamine (2.0 mL, 15.5. mmol) are added to a solution of bis(trichloromethyl) carbonate (1.55 g, 5.2 mmol) in CH2Cl2 (20 mL). The reaction mixture is allowed to warm to RT and stirred for another 1.5 h. For workup 1N HCl is added to the yellow suspension and the mixture is extracted with ethyl acetate. Drying (Na2SO4) of the combined organic exctracts, filtration and evaporation of the solvent affords the title compound. MS (LC-MS): [M+H]+=184.1. tR (HPLC, Waters Symmetry C18 column, 20-95% CH3CN/H2O/3.5 min, 95% CH3CN/H2O, 2 min, CH3CN and H2O containing 0.1% TFA, flow: 0.6 mL/min): 3.84 min.

Aufarbeitung

  1. customAt −78° C.
  2. extractionthe mixture is extracted with ethyl acetate
  3. customDrying
  4. filtration(Na2SO4) of the combined organic exctracts, filtration and evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-4142003187f249e9a9d2daa207c288d2
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807709B2

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